What School Could Be—and What Education Investors Get Wrong

Does this sound familiar? An Ivy League-educated philanthropist, who built his wealth from a career in technology, decides to champion education as his next cause—under the belief that today’s schools are not adequately preparing the next generation for the future.

We’re not talking about Bill Gates or Mark Zuckerberg. Rather, meet Ted Dintersmith, who has spent nearly 20 years as a partner at Charles River Ventures, an early-stage investment firm. These days, he’s no longer spending time in company boardrooms, but rather in schools and classrooms.

Look at the enormous amounts of money, effort and energy that have gone into charter schools. I have a huge amount of respect for some of them. But some are fraudulent. Many are test-prep factories.

Ted Dintersmith

In 2015, he funded and produced “Most Likely to Succeed,” a documentary that highlights how schools are experimenting with and embracing novel instructional models that get kids to take ownership of their learning. Afterward, he went on a roadtrip to all 50 states, visiting a couple hundred schools and classrooms to see what schools are doing today.

Dintersmith’s forthcoming book, “What School Could Be,” shares observations and lessons learned about innovation during those travels. Among them: authentic assessments, teacher agency and what he calls the “PEAK” principles that thriving students embody. He also offers some contrarian views about the value of college—and whether coding is really the career of the future that Silicon Valley would like us to believe.

The conversation has been edited and condensed for clarity. You can listen to a complete version below, or on your favorite podcast app (like iTunes or Stitcher).

Ted, sorry to break it to you. But you’re not the first well-off business guy trying to improve the state of education. So what makes you any different?

Dintersmith: When I’m meeting an educator, I always start by apologizing—because I know when they hear that somebody spent their career in business and now is interested in education, you can see the blood drain from their face.

What I think is different is I think I work really hard to understand what’s going on in schools. I’ve traveled all over the country. I went to all 50 states in 2015 and 2016, visiting a couple hundred schools. So instead of pronouncing what schools should do, I’m really trying to understand what schools are doing today that’s really working, and helping us amplify that so that people get energized and inspired by the kinds of progress we can make.

What really drove the trip was the urgency of two things. One, communicating the fact that we don’t have infinite amounts of time. While I’m humble about being limited in my classroom teaching experience, I’ve worked with the top entrepreneurs, and many people have a very hard time understanding just how fast the changes are happening and what it will mean when we live in a world where every routine job is gone.

That’s not the stuff of science fiction. That’s not 20, 30 or 40 years out. I think in 10 years there will be essentially no jobs left in the economy that don’t require some special skill by the employee hoping to fill that role.

You’re not the first to talk up the looming threat from machine intelligence and automation. How does that inform the skills that kids are going to need—or not need?

This is a fact: If it involves pattern recognition or following instructions, or if it’s something you can write a tight job description around, it’s probably going to be done by machine intelligence. If all you’re good at is memorizing content, replicating low-level procedures and following instructions, you will not be getting a job.

A lot of people who are my age naturally gravitate toward a vision of school as it was when they went to school. I think there’s just this sort of mantra that the key to success in U.S. education is better test scores and more kids off to four-year colleges. They never really step back and ask, “What’s in the curriculum? How aligned is it with what kids need to understand and be able to do today?”

What was the most unlikely source of innovation or inspiration across your travels? Is there one case study or school that comes to the top of your mind?

It’s not just one model that we need to pay attention to. It’s not one approach that everybody should look up to and try to emulate. All across the country, you can find innovative teachers doing the most amazing things with their students. Each case looks different: some are tech-driven, some are liberal arts-driven, some are who knows what.

But when you go one step below to look at what’s going on, these kids are working on challenges they think are important. They’re developing essential skillsets and mindsets, and they’re being trusted to manage their own learning. When you ask them about things, they don’t give superficial responses. They really understand it because they’ve had to apply it, or they’ve had to teach other kids what they’ve learned.

These kids won’t sprint through as much content as kids in a normal school will. But I think the evidence is pretty clear that most kids aren’t retaining what they’re learning. More times than not, when you ask a kid about what they learned a month ago or two months ago, it’s very hazy. If you just study something, cram for an exam, maybe power up with some Adderall, you might get a great exam score. But that is not the same as having really mastered it.

So how are these kids being given opportunities to apply and master skills?

I think the two most authentic forms of assessment boil down to: Can you teach somebody else what you’ve learned? Over and over again, people tell me you never learn anything as well as when you have to teach somebody else the same topic.

The second: Can you use it? Can you create something with it? Those are both things that drive students to really master what they’re studying. These skills are very directly observable, so it’s not as though you’re letting kids off the hook when it comes to accountability. You really do hold them to a very high standard of accountability.

One of the skills that people say kids will need is coding, and we’ve seen a concerted push to promote computer science. But you beg to differ.

What I believe is inane is when somebody says, “Knowing how to codes is a basic skill. It’s a 21st-century version of reading and writing and arithmetic.”

Coding jobs are not the explosive growth industry going forward. I think that a lot of the coding will be handled by artificial intelligence. Ten, 15 years ago people would say that everybody needs to know how to code in HTML because websites are going to be everywhere. Well, they were right about the websites, but they couldn’t have been more wrong about HTML.

To me, it’s not computer science. It’s computer literacy. It’s understanding and making yourself far more productive with the tools and resources that are out there. That’s what we need to teach—to encourage kids to learn and be confident that they can figure things out, whether they’re a philosophy professor, journalist, scientist or engineer.

When a school has a very traditional curriculum but then puts up a big celebration flag because it now offers AP computer science, that’s not the way forward.

There’s been a noticeable uptake in the amount of money going into education technologies. But do you think the problems in education are venture capital types of problems and opportunities?

Do I think the fact that a lot of people are thinking about education and willing to write checks to support it is a bad thing? Absolutely not. I think it’s a good thing.

I also think the focus should really should be on funding schools that produce future entrepreneurial adults, instead of entrepreneurial adults today funding obsolete schools.

But it’s hard to map this to great venture capital opportunities because from what I observed about innovative schools, no two are alike. They’re all doing different things that often don’t cost that much. They’re helping each kid in a different, very specific way to discover their strengths, learn more about their interest, and begin to gain the skills and confidence that they can use their life to make their world better.

If they are all quite different, I think it begs more for an innovation model in our school system than it begs for some massively-funded company doing the same for everybody. Not to use a hackneyed phrase, but “a thousand flowers blooming” model makes for a much harder market for venture capital.

What do most funders get wrong about education?

Look at the enormous amounts of money, effort and energy that have gone into charter schools. I have a huge amount of respect for some of them. But some are fraudulent. Many are test-prep factories. Many of them just say, “Boom. We will succeed because we get kids to do better on their test scores. We get more kids to graduate, and isn’t it great? All of our kids have to get a college acceptance letter as a graduation requirement.” I go to those schools, and the hallways are full of pennants and posters that basically say to these kids, “Your success is equivalent to your college placement. If you don’t go to college, you’re not a first-class citizen in America.”

This myth we have that these kids are going to college and immersing themselves in the most stimulating seminars and discovering the beautiful aspects of math around linear algebra, anthropology, all these things we think are happening with every kid cranking through college— that’s not the reality on the ground.

How are the most innovative teachers you saw supported, developed, encouraged, empowered to teach, perhaps, in a different way than they were taught?

A common denominator among these teachers, or the principals if it’s a school-wide transformation, is that they would all say somebody had their back. If a teacher wants to do something really out of the box, the principal will say, “There’ll be detractors, but I’ve got your back.” If a principal wants to change their school, the superintendent would say, “Parents may complain. The school board may be a worry. But I’ve got your back.”

I came away feeling like there’s a lot of pent-up innovation in the teaching force. If we actually highlight what they’ve accomplished, what they’ve learned, look objectively at the setbacks and not view those as a criticism of the teacher but as an opportunity to learn, that’s how change happens.